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Catalytic transformations of sulfur dioxide into organic sulfur compounds

  • Organic Chemistry
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The applications of catalytic transformations of SO2 into sulfur-containing organic compounds, reported in the literature, are briefly reviewed. The authors' studies in this field of chemistry,viz., the hydrosulfination of alkenes, the synthesis of γ-oxo sulfonesvia hydrosulfination, and the synthesis of aromatic sulfinic acids from diazonium salts, are summarized. Current results on the synthesis of the new sulfinato complex [Pd(SO2Ph)(Cl)dppp] and its hydrogenation to PhSO2H are presented, and a mechanism for the catalytic synthesis of sulfinic acids is proposed. The structure of ([Pd(μ-Cl)(dppp)l2 2+(SO4)2−·4SO2 salt is studied by X-ray diffraction analysis.

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References

  1. D. L. Lichtenberger, A. Rai-Chaudhuri, and R. H. Hogan, inInorganometallic Chemistry, Ed. T. P. Fehlner, Plenum Press, New York-London, 1992, Ch. 5, 223.

    Google Scholar 

  2. (a) W. Kitching and C. W. Fong,Organomet. Chem. Rev., A. 1970,5, (b) A. Wojcicki,Acc. Chem. Res., 1971,4 344; (c) A. Wojcicki,Adv. Organomet. Chem., 1974,12, 31.

  3. T. H. Coffield, J. Kozikowski, and R. D. Closson,J. Org. Chem., 1957,22, 598.

    Article  CAS  Google Scholar 

  4. W. R. Roper and L. J. Wright,J. Organomet. Chem., 1977, 142, C1.

    Article  CAS  Google Scholar 

  5. F. A. Hartmann and A. Wojcicki,J. Am. Chem. Soc., 1966,88, 846.

    Article  Google Scholar 

  6. M. Herberhold and A. F. Hill,J. Organomet. Chem., 1988, 353, 243.

    Article  CAS  Google Scholar 

  7. (a) R. F. Heck,Palladium Reagents in Organic Synthesis, Academic Press, London, 1985 (b) H. M. Colquhoun, D. J. Thompson, and M. V. Twigg,Carbonylation, Plenum Press, New York-London, 1991; (c) M. Beller, B. Cornils, C. D. Frohning, and C. W. Kohlpainter,J. Mol. Catal., 1995,104A, 17.

    Google Scholar 

  8. (a) H. S. Klein,J. Chem. Soc. Chem. Commun., 1968, 377; (b) US Pat. 3,399,146, 1968;Chem. Abstrs., 1968,69, 86367.

  9. US Pat. 4,808,697, 1989;Chem. Abstrs., 1989,111, 134938

    Google Scholar 

  10. E. Drent, J. A. M. van Broekhoven, and M. J. Doyle,J. Organomet. Chem., 1991,417, 235.

    Article  CAS  Google Scholar 

  11. (a)U. M. Dzhemilev, R. V. Kunakova, and Yu. T. Struchkov,Dokl. Akad. Nauk SSSR, 1980,260, 105 [Dokl. Chem., 1980 (Engl. Transl.)]; (b) U. M. Dzhemilev and R. V. Kunakova,J. Organomet. Chem., 1993,455, 1.

    Google Scholar 

  12. (a) J. Herwig, Ph.D. Thesis, RWTH, Aachen, 1994; (b) W. keim and J. Herwig,J. Chem. Soc., Chem. Commun., 1993, 1592; (c) J. Herwig and W. Keim,Inorg. Chim. Acta, 1994,222, 381; (d) J. Herwig and W. Keim, DE 4 329 932 A 1, 1995; (e) G. Pelzer, Diploma Thesis, PWTH, Aachen, 1995.

  13. W. Keim, J. Herwig, and G. Pelzer,J. Org. Chem., 1997,62, 422.

    Article  CAS  Google Scholar 

  14. (a) US Pat. 5,463, 145;Chem. Abstrs., 1996,124, 88123; (b) US Pat. 5,463, 144;Chem. Abstrs., 1996,124, 88122; (c) US Pat. 5,463, 146;Chem. Abstrs., 1996,124, 569940; (d) B. Cornils,Hydroformylation, Oxo Synthesis, Roelen Reaction, inNew Syntheses with Carbon Monoxide,11, Ed. J. Falbe, Springer, Berlin-Heidelberg-New York, 1980.

  15. J. Blum and G. Scharf,J. Org. Chem., 1970,35, 1895.

    Article  CAS  Google Scholar 

  16. G. Vitzthum and E. Lindner,Angew. Chem., 1971,83, 315.

    Google Scholar 

  17. W. A. Herrmann, C. Brossmer, T. Priermeier, and K. Öfele,J. Organomet. Chem., 1994,481, 97.

    Article  CAS  Google Scholar 

  18. A. Yamamoto,J. Organomet. Chem., 1995,500, 337.

    Article  CAS  Google Scholar 

  19. H. Pelzer and W. Keim,J. Org. Chem., 1997, in press.

  20. K. Kikukawa, T. Totoki, F. Wada, and T. Matsuda,J. Organomet. Chem., 1984,270, 283.

    Article  CAS  Google Scholar 

  21. M. Beller and K. Kühlein,Synlett, 1995, 441.

  22. F. H. Allen and O. Kennard,Chem. Des. Autom. News, 1993,8, 31.

    Google Scholar 

  23. E. Lindner, J. Dettinger, H. A. Mayer, H. Kühbauch, R. Fawzi, and M. Steimann,Chem. Ber., 1993,126, 1317.

    CAS  Google Scholar 

  24. G. M. Sheldrick,Acta Crystallogr., 1990,46A, 467.

    Google Scholar 

  25. G. M. Sheldrick,SHELXL-97: Program for the Refinement of Crystal Structures, University of Cambridge, Camridge (England), 1997.

    Google Scholar 

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Authors and Affiliations

  1. Institute of Technical Chemistry and Oil Chemistry of Rhine-Westfal Technical Higher School in Aachen, Worringerweg 1, D-52074, Aachen, Germany

    G. Pelzer, J. Herwig & W. Keim

  2. Max Planck Institute of Coal Research, Kaiser-Wilhelm-Platz 1, D-45470, Mülheim/Ruhr, Germany

    R. Goddard

Authors
  1. G. Pelzer
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  2. J. Herwig
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  3. W. Keim
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  4. R. Goddard
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Additional information

Institut für Technische Chemie und Petrolchemie der Rheinisch-Westfälischen Technischen Hochschule Aachen, Worringerweg 1, D-52074 Aachen, Deutschland.

Max Planck Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, D-45470 Mülheim/Ruhr, Deutschland.

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 933–942, May, 1998.

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Pelzer, G., Herwig, J., Keim, W. et al. Catalytic transformations of sulfur dioxide into organic sulfur compounds. Russ Chem Bull 47, 904–912 (1998). https://doi.org/10.1007/BF02498159

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  • DOI: https://doi.org/10.1007/BF02498159

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